RESEARCH ARTICLE
phenyl(4-(p–tolyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl)
methanone (3b) Yield: 60%; 58.0 mg, yellow solid; m.p=
(4-(4-chlorophenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
yl)(phenyl)methanone (3h): Yield: 73%; 76.9 mg, yellow
liquid; H NMR (400 MHz, CDCl3) δ 8.32 (d, J=7.5 Hz, 2H),
1
117.2–119.3 C; 1H NMR (400 MHz, CDCl3) δ 8.34 (d, J=
°
7.2 Hz, 2H), 7.68 (t, J=7.4 Hz, 1H), 7.55–7.46 (m, 3H), 7.41–
7.31 (m, 2H), 7.22 (d, J=7.8 Hz, 1H), 2.06 (s, 3H).13C NMR
(101 MHz, CDCl3) δ 181.2, 152.4, 146.4 (q, J(C-F) =39.2 Hz),
135.4, 134.8, 131.9, 131.1, 130.9, 128.8, 127.0, 126.9, 117.8 (q,
7.69 (t, J=7.4 Hz, 1H), 7.57–7.48 (m, 4H), 7.29 (d, J=8.6 Hz,
2H). 13C NMR (101 MHz, CDCl3) δ 181.2, 152.4, 146.6 (q,
J
(C-F) =39.5 Hz), 137.1, 135.0, 134.8, 131.1, 131.1, 129.8,
128.8, 128.2, 117.8 (q, J(C-F) =272.3 Hz). 19F NMR (377 MHz,
CDCl3) δ À 60.76. HRMS (ESI) calcd for C16H10ClF3N3O+[M+
H+]: 352.0459, found 352.0470.
J
(C-F) =272.1 Hz), 17.2. 19F NMR (377 MHz, CDCl3) δ À 61.97.
HRMS (ESI) calcd for C17H13F3N3O+ [M+H+]: 332.1005,
found 332.1012.
(4-(4-bromophenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
phenyl(4-(m–tolyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl)
methanone (3c): Yield: 66%; 63.8 mg, yellow solid; m.p=
yl)(phenyl)methanone (3i): Yield: 64%; 75.86 mg, yellow
1
°
solid; m.p=94.5–95.8 C; H NMR (400 MHz, CDCl3) δ 8.32
120.0–123.5 C; 1H NMR (400 MHz, CDCl3) δ 8.31 (d, J=
(d, J=7.3 Hz, 2H), 7.71–7.64 (m, 3H), 7.53 (t, J=7.8 Hz, 2H),
7.22 (d, J=8.6 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 181.1,
152.3, 146.5 (q, J(C-F) =39.5 Hz), 135.0, 134.8, 132.8, 131.6,
131.1, 128.8, 128.4, 125.1, 117.8 (q, J(C-F) =272.1 Hz). 19F
NMR (377 MHz, CDCl3) δ À 60.74. HRMS (ESI) calcd for
C16H10BrF3N3O+ [M+H+]: 395.9954, found 395.9957.
°
7.3 Hz, 2H), 7.68 (t, J=7.4 Hz, 1H), 7.53 (t, J=7.8 Hz, 2H),
7.43–7.36 (m, 2H), 7.14 (s, 2H), 2.42 (s, 3H). 13C NMR
(101 MHz, CDCl3) δ 181.3, 152.5, 146.6 (q, J(C-F) =38.9 Hz),
139.8, 135.1, 134.8, 132.5, 131.5, 131.1, 129.2, 128.7, 127.1,
123.8, 117.9 (q, J(C-F) =272.0 Hz), 21.3. 19F NMR (377 MHz,
CDCl3) δ À 60.82. HRMS (ESI) calcd for C17H13F3N3O+ [M+
H+]: 332.1005, found 332.1012.
(4-(4-nitrophenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
yl)(phenyl)methanone (3j): Yield: 53%; 57.6 mg, green solid;
1
°
phenyl(4-(o–tolyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl)
methanone (3d): Yield: 64%; 63.8 mg, yellow liquid; 1H NMR
(400 MHz, CDCl3) δ 8.30 (d, J=7.2 Hz, 2H), 7.70–7.64 (m,
1H), 7.54–7.49 (m, 2H), 7.32 (d, J=8.1 Hz, 2H), 7.21 (d, J=
8.3 Hz, 2H), 2.45 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 181.4,
152.6, 146.7 (q, J(C-F) =39.2 Hz), 141.1, 135.1, 134.8, 131.1,
m.p=159.7–160.2 C; H NMR (400 MHz, CDCl3) δ 8.42 (d,
J=8.8 Hz, 2H), 8.36 (d, J=7.5 Hz, 2H), 7.70 (t, J=7.4 Hz,
1H), 7.61–7.50 (m, 4H). 13C NMR (101 MHz, CDCl3) δ 180.8,
152.2, 148.9, 146.3 (q, J(C-F) =39.5 Hz), 138.0, 135.3, 134.5,
131.2, 128.9, 128.2, 125.0, 117.6 (q, J(C-F) =272.5 Hz). 19F
NMR (377 MHz, CDCl3) δ À 60.54. HRMS (ESI) calcd for
130.1, 129.9, 128.7, 126.5, 117.9 (q, J(C-F) =272.1 Hz), 21.4. 19
F
C16H10F3N4O3 [M+H+]: 363.0700, found 363.0703.
+
NMR (377 MHz, CDCl3) δ À 60.86. HRMS (ESI) calcd for
phenyl(5-(trifluoromethyl)-4-(4-(trifluoromethyl)phenyl)-
4H-1,2,4-triazol-3-yl)methanone (3k): Yield: 46%; 53.1 mg,
yellow liquid; 1H NMR (400 MHz, CDCl3) δ 8.34 (d, J=
7.3 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 7.70 (t, J=7.4 Hz, 1H),
7.58–7.47 (m, 4H). 13C NMR (101 MHz, CDCl3) δ 181.0,
152.3, 146.4 (q, J(C-F) =39.5 Hz), 135.8, 135.1, 134.7, 132.9 (q,
C17H13F3N3O+ [M+H+]: 332.1005, found 332.1010.
(4-(4-(tert-butyl)phenyl)-5-(trifluoromethyl)-4H-1,2,4-tria-
zol-3-yl)(phenyl)methanone (3e): Yield: 65%; 72.7 mg, yellow
1
liquid; H NMR (400 MHz, CDCl3) δ 8.29 (d, J=7.5 Hz, 2H),
7.68 (t, J=7.4 Hz, 1H), 7.53 (t, J=7.7 Hz, 4H), 7.26 (d, J=
8.4 Hz, 2H), 1.37 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 181.5,
154.0, 152.7, 146.8 (q, J(C-F) =39.3 Hz), 135.1, 134.8, 131.1,
129.7, 128.7, 126.4, 126.2, 117.9 (q, J(C-F) =272.2 Hz), 35.0,
31.2. 19F NMR (377 MHz, CDCl3) δ À 60.83. HRMS (ESI)
calcd for C20H19F3N3O+[M+H+]: 374.1475, found 374.1484.
J
(C-F) =33.2 Hz), 131.2, 128.8, 127.5, 126.8, 123.2 (q, J(C-F)
=
272.8 Hz), 117.7 (q, J(C-F) =272.3 Hz). 19F NMR (377 MHz,
CDCl3)
δ
À 60.67, À 62.83. HRMS (ESI) calcd for
C17H10F6N3O+ [M+H+]: 386.0723, found 386.0722.
(4-(2-fluorophenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
(4-(4-methoxyphenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
yl)(phenyl)methanone (3l): Yield: 50%; 50.3 mg, green solid;
1
°
yl)(phenyl)methanone (3f): Yield: 80%; 83.3 mg, yellow solid;
m.p=117.6–119.3 C; H NMR (400 MHz, CDCl3) δ 8.34 (d,
1
m.p=80.4–82.5 C; H NMR (400 MHz, CDCl3) δ 8.30 (d, J=
J=7.1 Hz, 2H), 7.73–7.23 (m, 8H). 13C NMR (101 MHz,
CDCl3) δ 181.1, 156.8 (d, J(C-F) =253.6 Hz), 152.4, 146.5 (q,
°
7.3 Hz, 2H), 7.67 (t, J=7.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 2H),
7.26 (d, J=8.8 Hz, 2H), 7.00 (d, J=8.9 Hz, 2H), 3.87 (s, 3H).
13C NMR (101 MHz, CDCl3) δ 181.5, 161.0, 152.7, 146.9 (q,
J
(C-F) =39.6 Hz), 134.9, 134.7, 132.8 (d, J(C-F) =7.8 Hz), 131.2,
128.7, 128.4, 124.9 (d, J(C-F) =3.9 Hz), 121.0 (d, J(C-F)
=
J
(C-F) =38.9 Hz), 135.1, 134.8, 131.1, 128.7, 128.0, 124.8, 117.9
13.7 Hz), 117.8 (q, J(C-F) =272.2 Hz), 116.7 (d, J(C-F) =19.0 Hz).
(q, J(C-F) =272.0 Hz), 114.6, 55.6. 19F NMR (377 MHz, CDCl3)
19F NMR (377 MHz, CDCl3) δ À 61.77, À 120.99.
δ À 60.97. HRMS (ESI) calcd for C17H13F3N3O2 [M+H+]:
+
(4-(3,4-dimethylphenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-
3-yl)(phenyl)methanone (3m): Yield: 58%; 60.0 mg, yellow
348.0954, found 348.0964.
1
°
(4-(4-fluorophenyl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
yl)(phenyl)methanone (3g): Yield: 61%; 61.3 mg, yellow
liquid; H NMR (400 MHz, CDCl3) δ 8.32 (d, J=8.0 Hz, 2H),
7.69 (t, J=7.4 Hz, 1H), 7.53 (t, J=7.7 Hz, 2H), 7.38–7.32 (m,
2H), 7.27–7.19 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 181.3,
163.5 (d, J(C-F) =252.3 Hz), 152.5, 146.7 (q, J(C-F) =39.6 Hz),
135.0, 134.9, 131.1, 128.9 (d, J(C-F) =9.3 Hz), 128.8, 128.5,
117.8 (q, J(C-F) =272.1 Hz), 116.7 (d, J(C-F) =23.5 Hz). 19F NMR
(377 MHz, CDCl3) δ À 60.86, À 108.50. HRMS (ESI) calcd for
C16H10F4N3O+ [M+H+]: 336.0755, found 336.0762.
solid; m.p=75.5–81.3 C; H NMR (400 MHz, CDCl3) δ 8.31
(d, J=8.0 Hz, 2H), 7.67 (t, J=7.4 Hz, 1H), 7.52 (t, J=7.7 Hz,
2H), 7.26 (d, J=7.9 Hz, 1H), 7.12–7.03 (m, 2H), 2.34 (s, 3H),
2.31 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 181.5, 152.6, 146.7
(q, J(C-F) =38.9 Hz), 139.7, 138.3, 135.1, 134.8, 131.1, 130.4,
130.1, 128.7, 127.3, 123.9, 117.9 (q, J(C-F) =272.0 Hz), 19.9,
19.7. 19F NMR (377 MHz, CDCl3) δ À 60.84. HRMS (ESI)
calcd for C18H15F3N3O+[M+H+]: 346.1162, found 346.1171.
1
(4-(naphthalen-1-yl)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-
yl)(phenyl)methanone (3n): Yield: 37%; 40.7 mg, yellow
Adv. Synth. Catal. 2021, 363, 1–11
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